The 1930s series of Bulldog Drummond movies had one where Drummond is injured in a car crash and Jack Pennington (played by comedian Jack Hulbert) is forced to stand in for him. It is considered part of the official series.

Hikonin Sentai Akibaranger, while the very title notes that it is an unofficial ("Hikonin") Super Sentai, it is produced by Toei, the same company behind the Super Sentai franchise. It includes cameos from previous Super Sentai characters... though they're only in AkibaRed's mind. It's also Hotter and Sexier, and comes with a disclaimer telling the "good kids" who normally watch Super Sentai to stay away.

The Five(ish) Doctors Reboot started as a fan film from former Doctor Peter Davison, but it became an official part of the 50th anniversary celebrations when Steven Moffat found out about it. In addition to being credited as an executive producer, Moffat plays himself as the villain of the piece.

Music

Although he doesn't legally have to, "Weird Al" Yankovic gets permission from the original artist before parodying one of their songs.

Tabletop Games

Critter-Tek, the funny animal parody of Battletech from Crunchy Frog Enterprises, was licenced by FASA and included an actual Battletech record sheet. A sticker on the cover said "Approved by FASA! Or at least they promised not to sue!"

Appearances of DC characters on the MAD television series can be seen as authorized, as the show is run by DC Comics. Mad even got a slot on DC Nation. (This could theoretically apply to the magazine as well.)

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